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Chapter 14: Q.21558-14-3P. (page 533)

How many 1H NMR signals does each compound show?

a.

b.

c.

d.

e.

f.

g.

h.

Short Answer

Expert verified

a. 2

b. 2

c. 2

d. 2

e. 4

f. 4

g. 5

h. 4

Step by step solution

01

NMR spectroscopy

Different types of proton NMR signals are observed in compounds due to the presence of different protons. The environment of these protons is affected by electron-withdrawing and electron-releasing groups.

02

 1H NMR signals in a, b, c, and d

a. The given compound has a plane of symmetry, as shown.

Plane of symmetry in a

Thus, the given compound has two types of protons, and it will give two signals.

b. The given compound has a plane of symmetry, as shown.

Plane of symmetry in b

Thus, the given compound has two types of protons, and it will give two signals.

c. The given compound has a plane of symmetry, as shown.

Plane of symmetry in c

Thus, the given compound has two types of protons, and it will give two signals.

d. The given compound has a plane of symmetry, as shown.

Plane of symmetry in d

Thus, the given compound has two types of protons, and it will give two signals.

03

 1H NMR signals in e, f, g and h

e. The given compound has four types of protons, and it will give four signals.

Structure of e

f. The given compound has four types of protons, and it will give four signals.

Structure of f

g. The given compound has five types of protons, and it will give five signals.

Structure of g

h. The given compound has four types of protons, and it will give four signals.

Structure of h

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Most popular questions from this chapter

Question. In the presence of a small amount of acid, a solution of acetaldehyde(CH3CHO) in methanol (CH3OH) was allowed to stand and a new compound L was formed. L has a molecular ion in its mass spectrum at 90 and IR absorptions at 2992 and 2941cm-1 . L shows three signals in its 13C-NMR at 19, 52, and 101 ppm. 1H-NMR spectrum of L is given below. What is the structure of L?

Question: As we will learn in Chapter 20, reaction of (CH3)2CO withLiC鈮�CH followed by affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600鈥�3200, 3303, 2938, and 2120cm-1 . D shows the following 1 H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?

Question: How could you use chemical shift and integration data in 1H NMR spectroscopy to distinguish between CH3OCH2CH2OCH3and CH3OCH2OCH3? The 1H NMR spectrum of each compound contains only singlets.

Question: Propose a structure consistent with each set of data.

a. A compound X (molecular formula C6H12O2) gives a strong peak in its IR spectrum at 1740 cm-1. The 1 H NMR spectrum of X shows only two singlets, including one at 3.5 ppm. The 13C NMR spectrum is given below Propose a structure for X.

b. A compound Y (molecular formula C6H10 ) gives four lines in its 13C NMR spectrum (27, 30, 67, and 93 ppm), and the IR spectrum given here. Propose a structure for Y.

Question: (a) How many 1H NMR signals does each compound show? (b) Into how many peaks is each signal split?
See all solutions

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